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Crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate
The crystal structure of the hexahydrate co-crystal of gallic acid and caffeine, C(7)H(6)O(5)·3C(8)H(10)N(4)O(2)·6H(2)O or GAL3CAF·6H(2)O, is a remarkable example of the importance of hydrate water acting as structural glue to facilitate the crystallization of two components of different stoichiome...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5946989/ https://www.ncbi.nlm.nih.gov/pubmed/29765767 http://dx.doi.org/10.1107/S2056989018004528 |
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author | Vella-Zarb, L. Baisch, U. |
author_facet | Vella-Zarb, L. Baisch, U. |
author_sort | Vella-Zarb, L. |
collection | PubMed |
description | The crystal structure of the hexahydrate co-crystal of gallic acid and caffeine, C(7)H(6)O(5)·3C(8)H(10)N(4)O(2)·6H(2)O or GAL3CAF·6H(2)O, is a remarkable example of the importance of hydrate water acting as structural glue to facilitate the crystallization of two components of different stoichiometries and thus to compensate an imbalance of hydrogen-bond donors and acceptors. The water molecules provide the additional hydrogen bonds required to form a crystalline solid. Whereas the majority of hydrogen bonds forming the intermolecular network between gallic acid and caffeine are formed by crystal water, only one direct classical hydrogen bond between two molecules is formed between the carboxylic oxygen of gallic acid and the carbonyl oxygen of caffeine with d(D⋯A) = 2.672 (2) Å. All other hydrogen bonds either involve crystal water or utilize protonated carbon atoms as donors. |
format | Online Article Text |
id | pubmed-5946989 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-59469892018-05-15 Crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate Vella-Zarb, L. Baisch, U. Acta Crystallogr E Crystallogr Commun Research Communications The crystal structure of the hexahydrate co-crystal of gallic acid and caffeine, C(7)H(6)O(5)·3C(8)H(10)N(4)O(2)·6H(2)O or GAL3CAF·6H(2)O, is a remarkable example of the importance of hydrate water acting as structural glue to facilitate the crystallization of two components of different stoichiometries and thus to compensate an imbalance of hydrogen-bond donors and acceptors. The water molecules provide the additional hydrogen bonds required to form a crystalline solid. Whereas the majority of hydrogen bonds forming the intermolecular network between gallic acid and caffeine are formed by crystal water, only one direct classical hydrogen bond between two molecules is formed between the carboxylic oxygen of gallic acid and the carbonyl oxygen of caffeine with d(D⋯A) = 2.672 (2) Å. All other hydrogen bonds either involve crystal water or utilize protonated carbon atoms as donors. International Union of Crystallography 2018-03-27 /pmc/articles/PMC5946989/ /pubmed/29765767 http://dx.doi.org/10.1107/S2056989018004528 Text en © Vella-Zarb and Baisch 2018 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Vella-Zarb, L. Baisch, U. Crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate |
title | Crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate |
title_full | Crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate |
title_fullStr | Crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate |
title_full_unstemmed | Crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate |
title_short | Crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate |
title_sort | crystal water as the molecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexahydrate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5946989/ https://www.ncbi.nlm.nih.gov/pubmed/29765767 http://dx.doi.org/10.1107/S2056989018004528 |
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